Toluene → Methyl 4-(diethoxyacetyl)benzoate

HRID 1099073Notes

Reaction equation

HRID 1099073 reaction equation
[O:1]=[CH:2][C:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)=[O:4].C([O-])([O-])[O:16][CH2:17][CH3:18].[C:21]1(C)C=CC=C[CH:22]=1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:21]([O:1][CH:2]([O:16][CH2:17][CH3:18])[C:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)=[O:4])[CH3:22]

Participants

5

Reactant 3

HCID 1140TolueneHCID 14276918Methyl 4-(2-oxoacetyl)benzoateHCID 53630039Ethylorthoformate

Product 1

HCID 59216300Methyl 4-(diethoxyacetyl)benzoateYield 82%

Reagents, catalysts & solvents 1

HCID 521998p-Toluenesulfonic acid monohydrateCatalyst

Procedure

A mixture of methyl 4-(oxoacetyl)benzoate (13.5 g, 0.0702 mol), ethyl orthoformate (29 mL, 0.18 mol), p-toluenesulfonic acid monohydrate (0.7 g) in toluene (150 mL) was heated under reflux for 2 h. After cooling, the solvent was removed under reduced pressure. The crude material was flash chromatographed on a silica gel column to afford the desired product (15.4 g, 82%). Analytical LCMS: (M+Na)+=289.0.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. temperatureAfter cooling
  4. customthe solvent was removed under reduced pressure
  5. customchromatographed on a silica gel column

Sources & evidence

ORD record
ord-a644d22e6dd44726bfdbd034db237a99
Source dataset
uspto-grants-2012_03
Patent number
US08143251B2

Reaction notes

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